The Vilna Gaon (and it is hinted at in Rashi bamidbar 22;21 ’im’) points out that there are two ways in Hebrew of saying ’with someone’ - either ’itto’ or ’itto, from the roots ‘im‘ and ‘itt‘.’ If there are two different words, each must mean something else (or just have 1 word!) so what is the difference between them? The Gaon reveals that the ‘itto’ root means to go with someone but not necessarily with the same motive or fervour, whilst the ’imo’ root means to go completely in sync with the other party - to share their motives, goals, and passion for the mission. This difference of ‘im’ and ’itt’ is also present in 2 of the sheva brachos we say at weddings; one ends ’mesameach chassan im hakallah’ whilst the other concludes ’mesameach chassan ve’challah.’ Why the different endings?
Since ‘im’ refers to simchah and growth together, whilst the ‘ve’ bracha concerns the individual simcha and growth of the bride and groom. And the ’ve’ bracha is put first, since this is the base - first there is individual growth motivated individually, and then comes the ability to grow and be sameach as a communal unit.

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